Flight Dilemma, What Would You Do?

This post may contain affiliate links from our advertising partners, such as American Express. Read my Advertiser Disclosure policy here. Additionally, some of the offers on this page may no longer be available through Deals We Like.

In a few weeks, my family is departing on a week long vacation to Cancun. This includes me, my husband, my 3 year old daughter, and my 7 month old son. I booked my flights months ago on Southwest when fares were ridiculously low. Using points, I am paying approximately 11,000 points per person roundtrip. Fortunately, I only have to pay for me and my daughter as I have the companion pass so my husband flies for free. I am also taking my son on as a lap child. Ultimately we are paying for 2 seats for 4 of us to actually fly, which is awesome!

For no reason at all, I looked up flights today on JetBlue since they have non stop flights Boston to Cancun. With my Southwest flights we have a layover in Baltimore, which isn’t ideal with kids, but far from a deal breaker. To my surprise, JetBlue actually has pretty low fares for our flight home! $151 per person or 8,000 points. Very comparable to the price paid with points on Southwest. Although, on JetBlue, we’d actually have to pay for 3 seats since no companion pass option, but would still have my son as a lap child.

So my big dilemma is which flight to take – Southwest or JetBlue. While we are 100% flying Southwest to Cancun, I am extremely undecided on which flight to take home. There are pros and cons for each of them and I am really torn. Of course my husband was half listening when I went through the benefits of each and told me it was ultimately my decision.

Pro’s / Con’s for JetBlue:

  • Pro: Non-stop flight
  • Pro: Leaves much later in the day which gives us half a day added to our vacation
  • Con: There are not many seats left and I wasn’t able to get 2 seats together, let alone 3 – while I am sure I’ll be able to get 2 seats together while at the airport, either my husband or I will be separated on the plane with one taking our daughter and the other our son
  • Con: Since there are not many seats available, the chances of being able to get my son an actual seat with his car seat is very low
  • Con: Since the flight leaves later in the day, it doesn’t arrive into Boston until 9pm – with my son that could be a real hit or miss
  • Con: Flying JetBlue will ultimately cost us about $300 more (this takes into consideration having to pay for another JetBlue seat, the difference in taxes (JetBlue is actually less), checked bag fees on JetBlue (Southwest is free) and a few other factors

Pro’s/Con’s for Southwest:

  • Pro: Flight gets in around 5:30pm which means night time for my son won’t be a total disaster
  • Pro: The flight still has a bunch of empty seats, so being able to bring a car seat on for my son and get him his own seat is extremely high (and since no assigned seating on Southwest, as long as there is one seat available then I am good)
  • Con: The flight leaves much earlier in the day and will require us to “wake up and go” which isn’t ideal
  • Con: We have about a 2 hour layover at Baltimore airport, although it allows us to sit down and eat lunch

While I love the concept of a non-stop flight and leaving later in the day, the extra $300 and the higher probability of my son not getting his own seat for the entire flight is holding me back.

What would you do?! I have 23 hours to cancel JetBlue if I want…  UPDATE – I decided to stick with Southwest!


The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. It depends on your financial situation how much $300 matters to you. It sounds like the potentially late arrival for your son could end up as a huge annoyance if it doesn’t work out, especially if the flight is delayed. I think I’d stick with the original plan this time given the price difference and room on the flight. Plus Baltimore isn’t a bad airport for a layover.

  2. Stick with the Southwest flights. $300 is a flight somewhere or a hotel night. $100 is my threshold for making a decision. What’s yours?

  3. Traveled with kids enough to know that the Southwest option would be less stressful and preferred. While you might get a few extra hours in Cancun with JetBlue, the cons of that would be just too much for me. Stick with Southwest.

  4. No brainer – JetBlue. Non-stop flights are much easier for kids let alone the multiple take and landings wth infants is annoying due to pressure changes. Flight short enough where an actual infant in arms won’t be so bad. Haven’t flown much southwest, but JetBlue may have Fred wifi / better entertainmemt on flight. No risk of missing connections/stressing about weather delays at connection. Any extra time in Cancun will be worth the $300!

  5. I’d stick with Southwest and spend the $300 to get over to Cozumel instead 🙂
    Seriously it will be less stress to just stay on what you have. The layover will also break it up for kids and stress. Maybe spend the $300 on a cheap roundtrip to Europe for later in the year.

  6. If, as I suspect, it’s going to be hell on earth if your son gets tired and has to be out, that’s easily enough to make this call for Southwest. You’ll get over the layover. And are getting a lot for the trouble.

  7. Is the $300 more in cash or points equivalent? If its points, a year ago I would have preferred to save on points and fly southwest but the points keep piling in and to me an extra day in Cancun is worth it. Plus it’s $300 more for an entire family, not 1 person.

    Also clearly not likely to happen, but when I flew home to Boston from Cancun last January with companion, our flight was delayed which caused us to miss our connection in Baltimore. They had to put us in a hotel room overnight (for about 5 hours) as they got us on a 6am flight which was not ideal.

    To avoid delays, missed flights, and potential cancellations alone I would now go with the direct flight.

    Also do you have mosaic status? You mentioned companion pass so did you get the Jetblue status match last year which is good through end of 2017? That would save you on bag fees and potentially get you all sitting together in more leg room seats.

    • @Mike – It is a combo of cash and points that make up the $300 difference. If this was a full extra day I’d agree, but it is really only getting me an extra morning, probably about 4 hours max.

      I did the status match to mosaic last year, but mine expired at the end of 2016.

  8. I worry about delays in the winter when taking a connecting flight. Love Jetblue nonstop and kids love the tv programming on Jetblue. Any chance you can get the Jetblue credit card in time to give you free bags ? Points for future flights. Good luck and where are you staying ??

  9. I’d definitely stay with Southwest. It’s cheaper, your family will be able to sit together, the earlier arrival will be easier on your son.

  10. Stick with Southwest. Leaving Cancun early isn’t going to be that big of a deal. Like what would you miss by leaving early, a leisurely breakfast? And $300 is $300!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.